Bromine → HCID 20392602, compound

HRID 1863317Notes

Reaction equation

HRID 1863317 reaction equation
[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:23]N1C(=O)CCC1=O.BrBr>C(Cl)(Cl)(Cl)Cl>[Br:23][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([O:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:22][CH:21]=2)=[CH:11][CH:12]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 3

HCID 24408BromineHCID 67184N-bromobutanimideHCID 20392615HCID 20392615, compound

Product 1

HCID 20392602HCID 20392602, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 0.80 g of methyl α-[p-(p-methylsulfonylphenoxy)phenyl]acetate and 0.49 g of N-bromosuccinimide in 12.5 ml of carbon tetrachloride is added several drops of carbon tetrachloride containing bromine. The mixture is stirred and refluxed for 3 days and the solvent removed under vacuum. The residue is dissolved in dichloromethane and filtered through a one inch by five inch column of silica gel. Evaporation of the filtrate gives the product as an oil.

Workup

  1. temperaturerefluxed for 3 days
  2. customthe solvent removed under vacuum
  3. dissolutionThe residue is dissolved in dichloromethane
  4. filtrationfiltered through a one inch by five inch column of silica gel
  5. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-97110cb4131f4907919fbd1095f58fdd
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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